Pteridine

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Pteridine
Pteridin - Pteridine.svg
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Names
Preferred IUPAC name
Pteridine [1]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C6H4N4/c1-2-9-6-5(8-1)3-7-4-10-6/h1-4H X mark.svgN
    Key: CPNGPNLZQNNVQM-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C6H4N4/c1-2-9-6-5(8-1)3-7-4-10-6/h1-4H
    Key: CPNGPNLZQNNVQM-UHFFFAOYAU
  • C1=CN=C2C(=N1)C=NC=N2
Properties
C6H4N4
Molar mass 132.126 g·mol−1
Melting point 139.5 °C (283.1 °F; 412.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Pteridine is an aromatic chemical compound composed of fused pyrimidine and pyrazine rings. A pteridine is also a group of heterocyclic compounds containing a wide variety of substitutions on this structure. Pterins and flavins are classes of substituted pteridines that have diverse biological roles. [2]

Synthesis of pteridine from 4,5-diaminopyrimidine and glyoxal Pteridinsynth2.svg
Synthesis of pteridine from 4,5-diaminopyrimidine and glyoxal

See also

Related Research Articles

Heterocyclic compound Cyclic compound that has atoms of at least two different elements as members of its ring(s).

A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of these heterocycles.

Nucleotide Biological molecules that form the building blocks of nucleic acids

Nucleotides are organic molecules consisting of a nucleoside and a phosphate. They serve as monomeric units of the nucleic acid polymers deoxyribonucleic acid (DNA) and ribonucleic acid (RNA), both of which are essential biomolecules within all life-forms on Earth. Nucleotides are obtained in the diet and are also synthesized from common nutrients by the liver.

Purine Chemical compound

Purine is a heterocyclic aromatic organic compound that consists of two rings. It is water-soluble. Purine also gives its name to the wider class of molecules, purines, which include substituted purines and their tautomers. They are the most widely occurring nitrogen-containing heterocycles in nature.

Pyrimidine is an aromatic heterocyclic organic compound similar to pyridine. One of the three diazines, it has the nitrogen atoms at positions 1 and 3 in the ring. The other diazines are pyrazine and pyridazine. In nucleic acids, three types of nucleobases are pyrimidine derivatives: cytosine (C), thymine (T), and uracil (U).

Pyridine Heterocyclic aromatic organic compound

Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one methine group (=CH−) replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. Today it is synthesized on the scale of about 20,000 tons per year worldwide.

Flavin group

Flavin is the common name for a group of organic compounds based on pteridine, formed by the tricyclic heterocycle isoalloxazine. The biochemical source is the vitamin riboflavin. The flavin moiety is often attached with an adenosine diphosphate to form flavin adenine dinucleotide (FAD), and, in other circumstances, is found as flavin mononucleotide, a phosphorylated form of riboflavin. It is in one or the other of these forms that flavin is present as a prosthetic group in flavoproteins.

Pterin

Pterin is a heterocyclic compound composed of a pteridine ring system, with a "keto group" and an amino group on positions 4 and 2 respectively. It is structurally related to the parent bicyclic heterocycle called pteridine. Pterins, as a group, are compounds related to pterin with additional substituents. Pterin itself is of no biological significance.

Pyrazine is a heterocyclic aromatic organic compound with the chemical formula C4H4N2. It is a symmetrical molecule with point group D2h. Pyrazine is less basic than pyridine, pyridazine and pyrimidine.

Pyridazine Organic compound based on the benzene ring, containing two nitrogen atoms in the ring

Pyridazine is a heterocyclic organic compound with the molecular formula (CH)4N2. It contains a six-membered ring with two adjacent nitrogen atoms, and is aromatic. It is a colorless liquid with a boiling point of 208 °C. It is isomeric with two other (CH)4N2 rings, pyrimidine and pyrazine.

Photolyase

Photolyases are DNA repair enzymes that repair damage caused by exposure to ultraviolet light. These enzymes require visible light both for their own activation and for the actual DNA repair. The DNA repair mechanism involving photolyases is called photoreactivation. They mainly convert pyrimidine dimers into a normal pair of pyrimidine bases.

ANRORC mechanism Reaction mechanism in ring systems

The ANRORC mechanism in organic chemistry describes a special type of substitution reaction. ANRORC stands for Addition of the Nucleophile, Ring Opening, and Ring Closure in nucleophilic attack on ring systems and it helps to explain product formation and distribution in some nucleophilic substitutions especially in heterocyclic compounds. It is widely used in the medicinal chemistry.

Hexazine

Hexazine is a hypothetical allotrope of nitrogen composed of 6 nitrogen atoms arranged in a ring-like structure analogous to that of benzene. It would be the final member of the azabenzene (azine) series, in which all of the methine groups of the benzene molecule have been replaced with nitrogen atoms. The two last members of this series, hexazine and pentazine, have not been observed, although all other members of the azine series have.

Dihydroxyphenylglycine

(S)-3,5-Dihydroxyphenylglycine or DHPG is a potent agonist of group I metabotropic glutamate receptors (mGluRs) mGluR1 and mGluR5.

4-hydroxybenzoate 3-monooxygenase

The enzyme 4-hydroxybenzoate 3-monooxygenase, also commonly referred to as para-hydroxybenzoate hydroxylase (PHBH), is a flavoprotein belonging to the family of oxidoreductases. Specifically, it is a hydroxylase, and is one of the most studied enzymes and catalyzes reactions involved in soil detoxification, metabolism, and other biosynthetic processes.

Alkylpyrazines are chemical compounds based on pyrazine with different substitution patterns. Some alkylpyrazines are naturally occurring highly aromatic substances which often have a very low odor threshold and contribute to the taste and aroma of various foods including cocoa, baked goods, coffee and wines. Alkylpyrazines are also formed during the cooking of some foods via Maillard reactions.

The Isay reaction is an organic reaction in which certain diaminopyrimidines are transformed into pterins by condensation with a 1,2-dicarbonyl compound, such as 2,3-butanedione. The reaction is named after Oskar Isay.

Iminocoumarins are a group of chemicals consisting of a coumarin with an attached imine group.

Fenarimol

Fenarimol, sold under the tradenames Bloc, Rimidin and Rubigan, is a fungicide which acts against rusts, blackspot and mildew fungi. It is used on ornamental plants, trees, lawns, tomatoes, peppers, eggplants, cucumbers and melons. It is mainly used to control powdery mildew. It works by inhibiting the fungus's biosynthesis of important steroid molecules.

Ethyl cyanoacetate

Ethyl cyanoacetate is an organic compound that contains a carboxylate ester and a nitrile. It is a colourless liquid with a pleasant odor. This material is useful as a starting material for synthesis due to its variety of functional groups and chemical reactivity.

2,3,4-Pentanetrione

2,3,4-Pentanetrione (or IUPAC name pentane-2,3,4-trione, triketopentane or dimethyl triketone) is the simplest linear triketone, a ketone with three C=O groups. It is an organic molecule with formula CH3COCOCOCH3.

References

  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 212. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
  2. Kritsky, M. S; Telegina, T. A; Vechtomova, Y. L; Kolesnikov, M. P; Lyudnikova, T. A; Golub, O. A (2010). "Excited flavin and pterin coenzyme molecules in evolution". Biochemistry. Biokhimiia. 75 (10): 1200–16. PMID   21166638.